Sodium Bicarbonate → 2-Cyano 3-(2,6-dichlorophenyl)propanoic acid

HRID 1285340Notes

Reaction equation

[C:1]([C:3](=[CH:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])[C:4]([OH:6])=[O:5])#[N:2].C(=O)([O-])O.[Na+].[BH4-].[Na+]>CO>[C:1]([CH:3]([CH2:7][C:8]1[C:9]([Cl:15])=[CH:10][CH:11]=[CH:12][C:13]=1[Cl:14])[C:4]([OH:6])=[O:5])#[N:2]

Participants

Conditions

Temperature: 18 °C

Procedure

92 g of 2-cyano 3-(2,6-dichlorophenyl)propenoic acid (Tetrahedron Lett., 1975, p.3643-4) are put into 860 ml of methanol and 285 ml of a 10% sodium hydrogen carbonate solution. This is cooled to 18° C. and the necessary quantity of sodium borohydride is introduced over a two and one-half hour period. The mixture is left for 2 hours at ambient temperature, then concentrated and acidified by adding 1N hydrochloric acid until a pH of 2.3. The solution is then extracted with ether and the organic layer is washed with water, dried on magnesium sulphate, filtered and evaporated. 82.4 g of 2-cyano 3-(2,6-dichlorophenyl)propanoic acid are obtained.

Workup

concentrationconcentrated
additionby adding 1N hydrochloric acid until a pH of 2.3
extractionThe solution is then extracted with ether
washthe organic layer is washed with water
customdried on magnesium sulphate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-0089e5f64709483cba3b68bc71463bca
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04567181

Reaction notes

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